Hydrochloric Acid → (2E)-3-(3-Thienyl)-2-propenoic acid

HRID 1360849Notes

Reaction equation

HRID 1360849 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].N1CCCCC1.[S:14]1[CH:18]=[CH:17][C:16](C=O)=[CH:15]1.Cl>N1C=CC=CC=1>[S:14]1[CH:18]=[CH:17][C:16](/[CH:1]=[CH:2]/[C:3]([OH:5])=[O:4])=[CH:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 681353-Thiophenecarboxaldehyde

Product 1

HCID 735793(2E)-3-(3-Thienyl)-2-propenoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

46 g of malonic acid and 2 ml of piperidine are added to 25 g of 3-thienaldehyde in solution in 100 ml of pyridine, and the mixture is heated at 100° C. for 4 hours. The reaction medium is cooled to 30° C. and it is poured over an aqueous hydrochloric acid solution (2N). The precipitate formed is filtered and it is rinsed with isopropyl ether to give, after drying, 30 g of a white solid.

Workup

  1. temperatureThe reaction medium is cooled to 30° C.
  2. customThe precipitate formed
  3. filtrationis filtered
  4. washit is rinsed with isopropyl ether
  5. customto give
  6. customafter drying

Sources & evidence

ORD record
ord-0d36de55ddbf4940b0a1a42cbc3c9ca6
Source dataset
uspto-grants-2011_02
Patent number
US07879889B2

Reaction notes

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